NO123852B - - Google Patents
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- Publication number
- NO123852B NO123852B NO2397/68A NO239768A NO123852B NO 123852 B NO123852 B NO 123852B NO 2397/68 A NO2397/68 A NO 2397/68A NO 239768 A NO239768 A NO 239768A NO 123852 B NO123852 B NO 123852B
- Authority
- NO
- Norway
- Prior art keywords
- group
- general formula
- nitrofuryl
- amidinofuran
- nitro
- Prior art date
Links
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- FUVVSNUVSKUJAS-UHFFFAOYSA-N furan-2-carboximidamide Chemical compound NC(=N)C1=CC=CO1 FUVVSNUVSKUJAS-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 241001502500 Trichomonadida Species 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 4
- 150000003230 pyrimidines Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- KWKCQUKDPDARNH-UHFFFAOYSA-N 5-nitrofuran-2-carboximidamide Chemical compound NC(=N)C1=CC=C([N+]([O-])=O)O1 KWKCQUKDPDARNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- ZJHZBDRZEZEDGB-UHFFFAOYSA-N 4-[5-(4-carbamimidoylphenyl)furan-2-yl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)O1 ZJHZBDRZEZEDGB-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- MVUMJYQUKKUOHO-UHFFFAOYSA-N ethyl 3-(dimethylamino)prop-2-enoate Chemical compound CCOC(=O)C=CN(C)C MVUMJYQUKKUOHO-UHFFFAOYSA-N 0.000 description 1
- BTQGDMLCRXCBGR-UHFFFAOYSA-N furan-2-carboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=CO1 BTQGDMLCRXCBGR-UHFFFAOYSA-N 0.000 description 1
- AFICWHSZTIGSPG-UHFFFAOYSA-N furan-2-yl(nitro)methanol Chemical class [O-][N+](=O)C(O)C1=CC=CO1 AFICWHSZTIGSPG-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- CNUPLDUFSMCTDT-UHFFFAOYSA-N propyl 3-(dimethylamino)prop-2-enoate Chemical compound CCCOC(=O)C=CN(C)C CNUPLDUFSMCTDT-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC040920 | 1967-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123852B true NO123852B (xx) | 1972-01-24 |
Family
ID=7435941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2397/68A NO123852B (xx) | 1967-06-23 | 1968-06-19 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3632584A (xx) |
| AT (1) | AT278822B (xx) |
| BE (1) | BE716946A (xx) |
| CH (1) | CH517773A (xx) |
| DE (1) | DE1695849A1 (xx) |
| DK (1) | DK120134B (xx) |
| ES (1) | ES355312A1 (xx) |
| FR (1) | FR1588826A (xx) |
| GB (1) | GB1236634A (xx) |
| NL (1) | NL6808832A (xx) |
| NO (1) | NO123852B (xx) |
| SE (1) | SE350046B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU471719A3 (ru) * | 1969-07-19 | 1975-05-25 | Шеринг Аг (Фирма) | Способ получени нитрофуриламиноалкоксипиримидина |
| BE754820R (fr) * | 1969-08-13 | 1971-02-15 | Schering Ag | Nouveaux derives de pyrimidine, leurs procedes de preparation et leurs |
| US3970648A (en) * | 1974-09-06 | 1976-07-20 | Diamond Shamrock Corporation | 2-[2-(5-Nitro-2-furyl)vinyl]-4-(anilino)quinazolines |
| AU2005287825A1 (en) * | 2004-09-23 | 2006-03-30 | Ulysses Pharmaceutical Products Inc. | Carbo- and hetero-cyclic antibiotics and use thereof |
-
1967
- 1967-06-23 DE DE19671695849 patent/DE1695849A1/de active Pending
-
1968
- 1968-06-12 AT AT565068A patent/AT278822B/de not_active IP Right Cessation
- 1968-06-13 DK DK275768AA patent/DK120134B/da unknown
- 1968-06-14 CH CH887668A patent/CH517773A/de not_active IP Right Cessation
- 1968-06-19 NO NO2397/68A patent/NO123852B/no unknown
- 1968-06-20 SE SE08420/68A patent/SE350046B/xx unknown
- 1968-06-21 BE BE716946D patent/BE716946A/xx unknown
- 1968-06-21 ES ES355312A patent/ES355312A1/es not_active Expired
- 1968-06-21 NL NL6808832A patent/NL6808832A/xx unknown
- 1968-06-21 FR FR1588826D patent/FR1588826A/fr not_active Expired
- 1968-06-24 US US739171A patent/US3632584A/en not_active Expired - Lifetime
- 1968-06-24 GB GB29965/68A patent/GB1236634A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH517773A (de) | 1972-01-15 |
| NL6808832A (xx) | 1968-12-24 |
| DK120134B (da) | 1971-04-13 |
| SE350046B (xx) | 1972-10-16 |
| DE1695849A1 (de) | 1971-05-13 |
| AT278822B (de) | 1970-02-10 |
| US3632584A (en) | 1972-01-04 |
| BE716946A (xx) | 1968-12-23 |
| FR1588826A (xx) | 1970-03-16 |
| ES355312A1 (es) | 1969-11-16 |
| GB1236634A (en) | 1971-06-23 |
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